


Breaking the Rules

by bellacatbee



Series: Prostitute and client verse [3]
Category: Supernatural
Genre: Alternate Universe - Prostitution, Anal Sex, Condoms, Dirty Talk, Drug Addiction, Emotionally Repressed, Internalized Homophobia, M/M, Oral Sex, Prostitution, Recovery - Drug Addiction, Safer Sex
Language: English
Status: Completed
Published: 2012-05-26
Updated: 2012-05-26
Packaged: 2017-11-06 01:39:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,077
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/413305
Author URL: https://archiveofourown.org/users/bellacatbee/pseuds/bellacatbee
Summary: <blockquote class="userstuff">
              <p>Castiel has rules. Only one client at a time, meet them in a public place first to get the look of them, always trust his instincts and always use a condom. Dean Winchester has him breaking those rules from the first time they meet.</p>
            </blockquote>





	Breaking the Rules

**Author's Note:**

> A continuation of my Prostitution verse telling Dean and Cas's side of the story.

The first time is a nothing, a one off. 

Castiel is so careful. His clients have to book him through his website. He doesn’t walk the streets and he always makes sure to leave a message on his answer phone with the exact address he’s going to in case anything happens. He also calls Michael with the same information. He calls Michael when he gets back too. They’ve been doing that since Castiel started in the game. He would have liked to have done something else but Michael is right that the money is good and Castiel has rules which mean he’s the one in charge. 

His rules are simple: He doesn’t see more than one person at a time. He meets them in a public place first because he trusts his instincts and if he doesn’t like a trick then he goes home, the money isn’t as important to him as his safety. And he always uses condoms. Castiel has a clean bill of health but he knows that not everyone is going to be like that. 

Because of his rules he doesn’t get a lot of new clients. He has the same men that he sees week in week out, a few he sees monthly. His website is updated with new information because Castiel is an escort and a prostitute. He’s happy to go on dates, happy to play pretend and sometimes that’s all his clients want. They’re bored business men with too much money who pay for him to go on dates with them, to keep them entertained. Castiel is good at listening to people; he’s good at being patient. He makes people feel as if they have his undivided attention.

The invitation to meet when it comes through is badly spelt. Castiel knows it’s probably someone who’s written the email while drunk. He gets a lot of that, men who can’t face up to what they really want. They trawl gay porn sites and escort services when they’re drinking, fantasizing about meeting up but they don’t want it when they’re sober. The thought of it disgusts them in the cold light of day.

Castiel still types back because occasionally he has met some CEOs with the worst spelling ever seen. Their secretaries are the ones who type up their memos and other important documents. He offers his services, gives his prices and then waits because he doubts that there will be a reply. 

When the message pings back asking for an hour, anal and suggesting they meet Castiel gives a time and a place and reminds he only does condoms. That should scare the guy off if he’s only fishing, it should spoil his fantasy or give him everything he needs to get off on. His new client however simply accepts the terms and Castiel is fine with that. He disconnects the chat after that. It doesn’t pay to get too involved before the money is on the table. Michael taught him that. 

**

The place Castiel asked for them to meet is a park and the time of day is the morning. There are lots of people there. They’re walking their dogs, playing with their kids, running. They have no idea that Castiel is sitting on the bench waiting to meet a trick. There is a hotel nearby that Castiel knows. It’s a nice enough place but he’s often used them because if there’s a little money under the table they’ll give him a room for an hour or two. Castiel prefers a nice, safe hotel where the staff know him and turn a blind eye to him then a motel. Motels are cheap. Castiel isn’t cheap. He needs to keep the right sort of air about him to get the right kind of clients. 

A man sits down on the bench next to him. He’s wearing jeans, a shirt and a battered old jacket. His hands are shaking. Castiel glances at him and then glances away. He has a nervous feeling in the pit of his stomach that this is his new client. He glances again. The man’s jaw is covered in stubble, his eyes are closed and Castiel wonders if he’s regretting this now he’s here. It wouldn’t be the first time someone backed out. Sometimes they wait right until Castiel is naked to call a stop to it or they get frustrated and can’t get it up and blame him. 

Castiel hates those moments. He hates feeling as if he’s in danger. 

He almost wants to stand up and leave, to walk away because something tells him that this client will be trouble. Then the man opens his eyes and looks at him and Castiel doesn’t look away. 

“Hi.” The guy says, his smile slow and his voice warm and Castiel nods hello because he can’t talk just yet. “I’m Dean,” The guy continues. “And you’re Cas, right? I recognise you from your website.” 

“Yes, I’m Cas.” Castiel agrees. His name on the website is a little softer, a little more personal because he liked his clients to feel as if they had a personal connection to him. It made them feel more at home with the transaction. Now he liked it because of the way Dean said his name, coated in honey, that made him feel like Dean knew every inch of his soul and that he liked what he’d seen. 

Dean smiles at him again. He puts a hand in his pocket and draws out the money. Castiel sighs softly under his breath. He had wanted this, the payment, to be a private act. It was the moment he disliked the most, second only to getting undressed in front of his client and offering his body to them. It made him feel vulnerable. He hates that feeling more than anything. He slips the bills away and then stands up.

“Come on. I’ve already got a room booked.” He says and Dean follows him. He walks a little bit behind Castiel, doesn't try to talk to him and Castiel turns occasionally to glance at him from the corner of his eye. If Dean left now he had the money so Castiel supposes he wouldn’t mind. Sex for pleasure had never been part of his job description but he would be sad if Dean disappeared now. 

Castiel used to be in trouble before he met Michael, he used to pop pills because it made him forget and it stopped him feeling. Sex was easier then. He didn’t care, he didn’t feel it. Michael made him stop because otherwise Castiel could have ended up just another body in an alleyway, dead from an overdose or worse. It makes the sex a little harder. Castiel has to be there for it, he can’t take something and drift off but he’s careful now. He’s earning money, not getting paid in things which will get him high and he prefers the person he is now he’s cleaned up.

He glances back again, half-smiling when he still finds Dean following him. He doesn’t think someone like Dean would have looked him up if Castiel was still taking drugs. Castiel can’t remember very well what those men were like back then but he remembers flashes of them and he knows they weren’t nice. Now he’s got a better class of clients and occasionally men like Dean turn up his life and Castiel feels a spark of something he thought he’d numbed with years of tranquilisers and then turning tricks. 

He’s never fallen for a client and he won’t. Clients are just money, they’re a source of income and nothing more but Castiel is still grateful when everything isn’t such a chore. He picks up his room key from the man at the desk, Chuck and then he and Dean are riding up in an elevator together to the fourth floor where most of the rooms are empty. Chuck has given them a room right down the hall and Castiel is painfully aware that Dean hasn’t tried to touch him yet. He unlocks the door and lets them into the room. He takes off his coat and hangs it on the back of the door as he shuts it while Dean sits down on the bed. 

“I’m not gay.” He starts and Castiel knows this speech by heart. “I just…I don’t know…I liked the way you looked and I’m curious.” Dean digs his hand back into his pocket, pulling out a fist full of condoms which he throws onto the bed beside him. “I don’t want to touch your dick. I just want to fuck you.”

Castiel nods. He knows Dean’s type. Self-loathing, self-hating gay or bisexual men who can’t accept that part of themselves. Dean wants what he wants but he can’t stand himself for it. Castiel wonders if he’s the first male prostitute Dean has visited, if he’s been working himself up to this or if he’s done this before. It doesn’t matter either way. Castiel doesn’t need to get off, he isn’t there to get off, he’s just there for Dean to enjoy. In a lot of ways this type of client is easy. He just wants to get himself off, get rid of his dirty fantasy about fucking a man and then he’ll run away and pretend to everyone that he’s straight until the next time that he can’t stand the fact that he doesn’t have a man’s hard body in his bed at night. Then he’ll come back to Castiel or some other man he sees online or on the corner of the street. 

“That’s fine.” He says. “I know you’re not gay, Dean.”

Dean visibly relaxes at the verbal reassurance and then he’s pulling off his clothes, jacket on the floor, t-shirt over the arm of a chair and Castiel starts undressing as well. No foreplay it seems and he’s glad he took the time to stretch and lube himself before meeting Dean. He learned the hard way to always be prepared. Some men don’t even realise that Castiel needs a bit of work before he can accommodate them, especially the ones who mostly fuck women. He guesses Dean is that type. He might even be the first man Dean’s ever fucked. If Dean goes through with it. He looks pretty confident currently while he’s stripping and Castiel can’t stop looking but when Castiel starts to take of his own clothes Dean sits back down on the bed, averting his gaze. 

It happens sometimes. “Dean,” He says, kneeling naked on the carpet in front of the other man. “We don’t have to do this, you know. I know you’re not gay.” His eyes flicker up to Dean’s face and he gages his reaction. Dean looks frustrated, not relieved. “Or maybe I could use my mouth? It will be extra.” Castiel doesn’t do freebies. Everything is paid for. Everything costs something. 

Dean nods slowly. “Yeah, I…I’ve got a bit more cash on me.” He spreads his legs, letting Castiel between them and Dean’s cock his half-hard. He wants to get it up, Castiel knows that, but Dean must feel shame, a sick feeling twisting in his stomach because he knows that what he’s doing is wrong. Castiel wonders if Dean has a girlfriend or a wife at home or if it’s his parents he’s worried about upsetting. Castiel can remember all those feeling vividly. It was why he’d had to escape, why he’d had to dull those pains. Michael helped him to accept himself, helped him to give them up. Castiel wouldn’t say he’s proud but he’s out and he knows who he is now and that he doesn’t owe himself to anyone else. It took him a long time to get there though so he doesn’t begrudge Dean what he’s feeling.

He wraps his fingers around Dean’s cock, stroking him firmly, making sure that Dean gets used to the feeling of his hand, realises that this is a man touching him so he can’t close his eyes and fake something else and Dean is hard for him in a few seconds. Castiel closes his eyes, bowing his head and takes the head of Dean’s cock in his mouth, tongue flickering across the slit and Dean groans above him. A second later fingers curl in his hair, trying to tug him forward, trying to force more of the cock into his mouth and Castiel lets him because Dean will be paying for this and he can direct Castiel however he likes. 

He swallows down Dean’s length, showing off more than anything because if this is the first time Dean’s been with a man then Castiel wants to blow his mind, he wants Dean to remember this and remember how good it was and not remember the shame of it. Michael always says that their job is to make sure their clients live out their fantasy without interruption. Castiel bobs up and down, letting Dean slip a little deeper each time, deep-throating him because Castiel destroyed his gag-reflex a long time ago, doing something he can’t remember but its worked out for the best because it’s a good trick and most guys have only ever seen it done in porn. True to form Dean bucks up, hips stuttering in the air before he comes and as the come hits the back of his throat Castiel realises that he broke his own rule. He forgot to use a condom. 

He whips back away from Dean, scrambling to his feet and runs into the bathroom. He coughs up into the sink and knows that this has probably spoilt the moment but he washes his mouth out, feeling so angry with himself because the condoms were right in front of him on the bed beside Dean and he still didn’t use them, he still forgot them because he was in such a rush to make Dean happy. 

He trails back into the other room slowly, angrily. Dean is watching him like a wounded animal, as if he doesn’t trust what Castiel will do next.

“I don’t usually come that fast.” He says and Castiel almost wants to laugh because Dean doesn’t seem at all put off by the fact that Castiel was practically throwing up his spunk in the bathroom. He just seems angry with himself that he didn’t have the stamina he thought he did. Castiel doesn’t judge. Some guys do come quickly; some guys take forever to get warmed up. Dean’s probably overloaded from the fact that he’s finally getting what he wants in the bedroom. 

“I know, Dean.” He says, his voice broken and he can see Dean’s cock giving a twitch of interest. He crosses to the bed and sits down next to Dean. “Do you still want to fuck me?” The words sound so vulgar and Castiel doesn’t like them but blunt is the best way. All the information is there. No one gets hurt. He’ll remember his rules now. 

Dean nods and his cock his hardening again. Castiel is glad. He’s actually pleased that Dean isn’t spent and ready to go yet. The feeling catches him by surprise but he doesn’t dwell on it. He picks up a condom and rips it open. A few quick strokes and Dean is hard again. Castiel rolls the condom down over his shaft, gives Dean’s balls a playful tug and gets his hand slapped away for his trouble. Dean might be close again or he just might not enjoy being touched when he hasn’t invited it but whatever the reason is Castiel is apologetic and Dean forgives him, rolling him over onto his stomach.

“Want to fuck you like this.” He pants, leaning over Castiel’s shoulder, bracing his arms on either side of Castiel so he’s firmly trapped under Dean. Dean may have control issues, Castiel guesses. He’s become good at guessing the psychology of his clients. Dean wants to be in charge and he doesn’t like it when he’s not. That’s fine by Castiel. He likes to be ordered around. It makes things easier; it takes the pressure from him. He can follow orders and lose himself. 

“That’s good.” He says, licking his lips that are suddenly dry. “You can have me like this.” He hopes Dean won’t want him to talk. Castiel is naturally quiet. He isn’t a screamer and he can’t fake it like some people can. He can’t get himself worked up by description and his own dirty talk vocabulary is limited and repetitive. Dean bites his shoulder then and Castiel whimpers. If Dean leaves a mark he has to pay. That was on the price list. Dean should have read it or maybe he had been drunk when they were talking.

“No marks.” Castiel gasps, just to remind him but Dean bites harder. Castiel remembers that Dean probably has control issues and he whimpers again. “Please, Dean.” That gets him to let up and Castiel wriggles a little, trying to remind Dean what he’s really there to do. Dean doesn’t take much reminding. He shoves Castiel’s legs apart with his knee, sliding over him until he’s pressing up tight against Castiel’s back. Castiel’s surprised Dean doesn’t want him on hands and knees, the angle of penetration would be easier but Dean said he didn’t want to touch Castiel’s dick and this way his dick is hidden from sight, sandwiched between the bed and his stomach. Castiel hates that he’s hard for Dean but he is. The biting pushed him over the edge. It looks good too, he knows, that he can get hard but Dean isn’t even the kind of client who’d appreciate that. 

The press of Dean’s cock reminds him what’s about to happen and Castiel concentrates on relaxing. Dean is surprisingly gentle. He eases his way in, letting Castiel get adjusted to the head of his cock before sliding deeper inside him, filling him with the rest. Castiel knows that its likely Dean’s fucked girls like this, just the same way he’s fucking Castiel know – face down so he can live out his own dreams of who he’s really taking. 

Dean lies on top of him, pressing him down into the bed and he has to press his knees either side of Castiel’s slim hips to gain any traction. Dean’s cock is only sliding in half way, not even filling him up completely but Dean seems content to fuck him like that. He rolls his hips slowly, pushing in then almost pulling out. For everything he’d been before Dean is a surprisingly gentle lover. He’s taking his time, his thrusts are languid and Castiel reasons that maybe he wants to make himself last but then he suspects that Dean enjoys sex and he likes spinning it out, likes making the most of it. 

Castiel prefers people who come roughly and quickly and get it over with. The fact that Dean won’t be one of those men leaves him rubbing himself into the bed, trying to get himself off because Dean has made him hard but Dean has also made it clear that he won’t help Castiel to get off. Because his strokes are shallow Dean’s not getting deep enough to give Castiel want he needs, Castiel won’t be able to come from prostate stimulation like he’s done a few times before. Sometimes it takes him by surprise, usually at the end of the day when he’s already so overworked that someone just hits him the right way and he’s spurting everywhere, unable to hold it back because his body’s overstimulated but Dean isn’t going to give him anything like that so Castiel has to fuck into the bedclothes to try and gain any amount of friction. It forces him back onto Dean’s cock and Dean groans appreciatively.

“You’re so desperate for it, aren’t you?” He whispers and Castiel buries his face in the pillow so he won’t have to talk back. It doesn’t stop Dean though. “Offering yourself up to anyone. You don’t care who it is as long as you get the money. I almost didn’t come. Almost couldn’t but then I thought about your eyes. Fuck, you’ve got pretty eyes.” He’s babbling really, talking about nothing but Castiel likes the way his voice is low, rough with lust and the way Dean keeps talking about him. He knows Dean wants to call him a whore, it’s hidden there on the edge of everything else he’s saying but Dean doesn’t seem able to form the words. He just tells Castiel he’s pretty and keeps slowly fucking him. It’s like a pleasurable torture and Castiel doesn’t know what to do. He’s caught between pleasure and pain, so hard now but nowhere near the edge. He’s being kept hard, being forced to listen to Dean because Dean doesn’t seem to care that no one is talking back to him, he’s getting off on whatever he’s saying and now to Castiel’s slight embarrassment he realises that he’s getting off to Dean’s words as well. 

“Please.” He whispers, glad that the sound if muffled by the pillow but he feels Dean’s hand stroking down his back. He bucks his hips up, hoping that Dean realises that he likes it, that it isn’t pain he’s feeling but something sweeter. 

“You are such a cocktease.” Dean grumbles, shifting and then he’s pulling out and Castiel bucks up again because he’s so empty now. Dean shifts on the bed and then all at once Castiel’s hips are being pulled up and Dean has him face down and ass up and he’s back inside with one stroke that send Castiel reeling because its finally deep enough. He squirms, not touching himself because he doesn’t want to upset Dean and he doesn’t know if Dean will take it too well if Castiel starts jerking himself off so he concentrates instead on making sure Dean hits the right spot every time and he does. He works Castiel up, keeps a steady, slow rhythm but with each push he’s brushing just the right place and Castiel can feel the orgasm building inside him. 

“You gonna come?” Dean asks him and Castiel nods because he can’t speak, he’ll just get a mouthful of pillow, but he is. Dean’s thrusts become a little faster, a little more forceful and Castiel is so grateful to him because Dean knows just how to push him over the edge. Castiel feels like his flying and orgasmic bliss is nearly as good as being high had been but its better because this will never kill him, this will never be something Michael has to wean him off and it will never be something Castiel can become addicted to because it’s so rare. 

He wants to just slide down into the bed but Dean’s hands grip him, keep him up right and Dean keeps fucking him right on through. Castiel feels every after shock and his spent cock leaks the last few drops he has in him which Dean rings from his body. The fact that Dean can still keep going, doesn’t show any sign of stopping, makes Castiel think that he was probably right that he doesn’t usually come as fast as he did when Castiel had him in his mouth. His stomach draws up tightly, remembering how close he came to almost swallowing and no matter how careful he thinks he was he’ll have to go to the clinic. He doesn’t want to think that Dean has anything but it’s always better to be safe than sorry. 

He drifts into a comfortable numbness, his body absorbing every little tremble of pleasure that comes from Dean fucking him. He doesn’t know how long it is, it feels like hours but Castiel knows that’s impossible. He knows if he checks the clock and they’re over their hour then Dean is paying more. He just forgets how to feel time when he’s like this. It’s a scary feeling but also a liberating one. There is no outside world, there is nothing but what is here and happen between his spread thighs. 

Finally Dean’s thrusts become a little ragged, he doesn’t draw out as much, he just pushes in, pushes in until Castiel wants to tell him that he’s full, that it’s all he can take and then Dean jerks and Castiel knows that means he’s come. Dean slides out of him slowly, releases his hold on him and Castiel finally collapses into the bed. His whole body aches. He’s grateful he isn’t seeing anyone till the evening because he needs to take a long bath, needs to clean himself up and he needs to take some painkillers or tonight is going to be rough. 

“That was so fucking good.” Dean says, rolling onto his side next to him and Castiel peeks at him long enough to see Dean pulling the condom off his spent cock and throwing it into the wastepaper basket. That will be a fun gift for Chuck and the house keeping staff later. Castiel just makes a noise of agreement, not trusting himself to talk. Dean looks at him strangely for a moment, as if he wants to say something more but then he’s up and getting dressed. 

Castiel forces himself to sit up. He runs a hand through his hair, knows that he must look a mess because he’s fucked out and he has come painted over his stomach. He wouldn’t expect Dean to be the type of guy who’d want to stay and cuddle. “The money for the blow job.” He croaks out in case Dean forgets. 

Dean pulls out his wallet and he throws the bills at Castiel, letting them flutter down around him and into his naked lap. His lip is curled in s sneer. “Yeah, that was all you wanted wasn’t it. Just the money. Fuck you, Cas.” He’s storming out the door before Castiel quiet knows what to say. He sighs, collects the money and tidies it away neatly. Dean paid exactly the amount advertised. Castiel is used to people who find it hard to disassociate the sex they just had with the fact that they paid for it. It’s why he prefers to get the money up front. That and the fact that he can’t be fucked and then left without recompense for the act. Dean isn’t the first man to get upset when Castiel broke the fantasy but he is one of the only one’s its hurt with. People have called him names, they’ve spat at him, degraded him, some of them have even frightened him but Dean’s angry, tight words sting a lot more than if he’d just called Castiel a slut and had done with it. 

He lets himself into the shower because he wants to look decent when he goes downstairs. His whole body aches in a way Castiel hasn’t ached in a long time. He can normally take it but when he checks his watch he realises that Dean used almost their whole hour just slowly fucking him. It makes Castiel’s head spin. A guy like that shouldn’t need to buy a prostitute. He’s handsome, he has skills but Michael always says that assuming someone like that is confident or happy with what they want is the worst assumption to make. For some reason Dean can’t fuck the men he wants and that means he needs someone like Castiel. He just hates the fact that he’s paying for it. 

Castiel washes himself all over, feelings the soothing heat of the shower on his muscles which start to relax and he fingers his shoulder and finds the mark Dean left there. It’s not deep and it should have faded away before his evening appointment. 

He doesn’t expect to see Dean again. Dean might have been something interesting but Castiel is almost certain he will be a one off. He upset Dean when he asked for the money and he doubts that upset is something Dean will take lightly. He seemed like the sort to hold grudges. 

In the end its two months before he hears from Dean again and Castiel has pushed him to the back of his mind and almost forgotten him by then. Other men have come and gone, other men have fucked him and Castiel has even come once or twice with them but when Dean’s message springs up on the screen everything they shared together in the hotel room rushes back to Castiel and he squirms eagerly in his chair. 

“What do you want?” He types and attaches his price list again in case Dean has deleted their last correspondence in a fit of temper given their last meeting. 

“Anal. Bareback.” Comes the reply and Castiel’s breath catches in his throat.

“I don’t do bareback.” He replies quickly. “Condoms only. I have rules.”

Dean’s response is fast. “You already broke those rules for me. Break them again. I want to come inside you.”

Castiel’s fingers hover over the keys and he knows he should just type ‘no’ and close down the chat. Dean’s been warned. Castiel made a mistake and one he’s lucky to have walked away from with a clean bill of health but he resists. He remembers Dean’s green eyes, remembers the bite to his shoulder, remembers how Dean bought him over the edge and left him a trembling wreck on an anonymous hotel bed. He remembers Dean’s anger, remembers thinking they’d never meet again. Dean is obviously cycling. Castiel doubts he’ll have gone to another prostitute between the last time they met and now. Dean has probably been ploughing himself into women and drink and work or whatever else he has to mask his sexuality and his crisis over it. It’s Castiel then that he can’t stay away from, Castiel who finally tempted him to make that move from fantasy to reality. 

Castiel knows if it wasn’t him then it would have been someone else because you can’t go on denying your true nature forever but he doesn’t want to focus on that for the moment. He wants to focus on the words Dean said to him, how hard he got Castiel and how gently he moved when he was in him, as if Castiel was his lover and not a whore he’d hired. 

When he finally replies he simply types. “Where do you want to meet? Bareback will be extra.” and waits for Dean to send him the directions.


End file.
